Yellowish vat dyestuffs



Patented June 24, 1930 warren stares PATENT oFFic GEORG KRANZLEIN, HEINRICH GREUNEYAND HEINRICH voLLMANN, or HOCHST-ON- THE-MAIN, GERMANY, AssIeNoRs o GENERAL ANILINE WoRKs, me, 015 NEW YORK, N. Y., A CORPORATION OF DELAWARE yELL-owrsn VAT DYESTUFFS No Drawing. Original application filed February e, 1925, eel-m1 No..7,3'90, and. in Germany February 16, 1924. Divided and this application filed November 27, 1925. Serial No. 71,708.

In German Patents Nos. 365,902 and 368,168 to 368,172 there are described condensation products which are obtainable by subjecting para-hydroxyphenazines or naphthosultam-3.t-phenazines to reaction with Q-chloro-lA-quinones or their substitution products or with mono-or dichlorol-naphthosultamquinone.

WVe have now found that the compounds of the general formula:

SO2-NH wherein X stands for a substituent of the group consisting of hydrogen and halogen,

are capable of reacting in the presence of an organic solvent with a 1.4-quinone which is substituted in the 2 and 3 positions by hydrogen, and that the condensation products thus obtainable can be converted into valuable dyestuffs by a subsequent treatment with an alkaline oxidizing agent.

The following examples illustrate our indyes from the vat bright yellow tints with v a greenish hue. It is a striking fact that 2- chlornaphthosultam-3.4-phenazine does not thoquinone not even when the methods indicated in the said German patents are employed (addition of metallic copper and anhydrous sodium acetate).

The reactions above described may be represented graphically as follows:

(2) 30 parts of naphthosultam-3.4-phena- V zine of the most probable formula:

S o -NH and 11 parts of benzoquinone are heated to undergo any reaction with 2.3-dichlornaphboiling innitrobenzene for 15 minutes, lhe n1 condensation product which separates constitutes a body crystallizing in reddish-brown prisms, which dyes from an olive vat, after exposure to air, khakicolored tints. By treating the said condensation product with hypochlorite solution a yellow dye-paste is obtained which is most suitable for the preparation of color-lakes.

(3) parts of naphthosultam-3. l-phenazine, 36 parts of B-hydroxynaphthoquinone, 30 parts of acetic anhydride and 300 parts of nitrobenzene are heated to boiling until the formation of the dyestutt is complete. After cooling the product is washed with alcohol and the condensation product, if required, subjected to an after-treatment with an alkaline oxidizing agent.

. This application is a division of our application Serial Number 7,390, filed February 6th, 1925.

\Veclaim:

l. The-process which comprises heating 2- chloro-naphthosultam-3.4E-phenazine with a lA-quinone which is substituted in the 2 and 3 positions by hydrogen, in the presence of an organicsolvent andtreating the condensation product with an alkaline oxidizing agent.

2. The process which comprises heating 2- chloro-naphthosultam-3.4-phenazine with a lA-quinone which is substituted in the 2 and 3 positionsby hydrogen, in the presence of nitrobenzene and treating the, condensation product with an alkaline o'xidizing agent.

3. The process which comprises heating 2-chloro naph'thosultam-3. l-phenazine with 1.4-naphthoquinone, in the presence of nitrobenzene and treating the condensation procluct with an alkaline oxidizing agent.

4. The process which comprises heating 6. The process which comprises heating a compound of the general formula:

SO2-NH Gnone KRANZLEIN. HEINRICH GREUNE. HEINRICH VOLLMANN.

tures.

2-chloro-naphthosultam-3.4-phenazine with V 1.4-naphthoquinone, in the presence of nitrobenzene at a temperture of 160 C. to 170 C. and treating the condensation product with hypochlorite solution.

5. The process which comprises heating a compound of the general formula:

IUIN

wherein X stands for a substituent of the group consisting of hydrogen and halogen, with a lAl-quinone which is substituted in the I 

